#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:13:01 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178840 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/94/4109457.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4109457
loop_
_publ_author_name
'Natalia F. Blank'
'Jillian R. Moncarz'
'Tim J. Brunker'
'Corina Scriban'
'Brian J. Anderson'
'Omar Amir'
'David S. Glueck'
'Lev N. Zakharov'
'James A. Golen'
'Christopher D. Incarvito'
'Arnold L. Rheingold'
_publ_section_title
;
 Palladium-Catalyzed Asymmetric Phosphination. Scope, Mechanism, and
 Origin of Enantioselectivity
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6847
_journal_page_last               6858
_journal_paper_doi               10.1021/ja070225a
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C23 H30 F3 P'
_chemical_formula_weight         394.44
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                72.103(3)
_cell_angle_beta                 87.885(3)
_cell_angle_gamma                87.702(3)
_cell_formula_units_Z            2
_cell_length_a                   9.5300(13)
_cell_length_b                   10.3374(15)
_cell_length_c                   11.8010(17)
_cell_measurement_reflns_used    3167
_cell_measurement_temperature    218(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.30
_cell_volume                     1105.1(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      218(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5380
_diffrn_reflns_theta_full        22.50
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.9554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       slabs
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.198
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0900
_refine_ls_shift/su_max          0.574
_refine_ls_shift/su_mean         0.066
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0864P)²+1.1872P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2158
_refine_ls_wR_factor_ref         0.2246
_reflns_number_gt                2478
_reflns_number_total             2877
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja070225asi20070309_123028_6.cif
_cod_data_source_block           glu142
_cod_database_code               4109457
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P 0.34240(14) 0.49117(13) 0.40467(12) 0.0532(5) Uani 1 1 d .
F1 F 0.6076(5) -0.0379(5) 0.2407(6) 0.156(2) Uani 1 1 d .
F2 F 0.7767(5) 0.0939(5) 0.1932(4) 0.1269(16) Uani 1 1 d .
F3 F 0.7564(5) -0.0379(4) 0.3651(4) 0.1279(17) Uani 1 1 d .
C1 C 0.1862(5) 0.5204(5) 0.3108(4) 0.0523(13) Uani 1 1 d .
C2 C 0.1671(6) 0.6507(5) 0.2295(5) 0.0623(14) Uani 1 1 d .
C3 C 0.0504(7) 0.6784(6) 0.1606(5) 0.0798(18) Uani 1 1 d .
H3A H 0.0384 0.7660 0.1065 0.096 Uiso 1 1 calc R
C4 C -0.0498(7) 0.5848(7) 0.1666(6) 0.0833(19) Uani 1 1 d .
C5 C -0.0284(6) 0.4560(6) 0.2452(5) 0.0698(16) Uani 1 1 d .
H5A H -0.0952 0.3898 0.2503 0.084 Uiso 1 1 calc R
C6 C 0.0867(5) 0.4210(5) 0.3160(5) 0.0547(13) Uani 1 1 d .
C7 C 0.2722(7) 0.7627(5) 0.2126(5) 0.0798(18) Uani 1 1 d .
H7A H 0.3270 0.7389 0.2862 0.096 Uiso 1 1 calc R
C8 C 0.3718(9) 0.7673(10) 0.1155(10) 0.162(5) Uani 1 1 d .
H8A H 0.4369 0.8396 0.1074 0.243 Uiso 1 1 calc R
H8B H 0.3217 0.7844 0.0420 0.243 Uiso 1 1 calc R
H8C H 0.4234 0.6810 0.1322 0.243 Uiso 1 1 calc R
C9 C 0.2069(11) 0.8998(7) 0.1976(11) 0.180(5) Uani 1 1 d .
H9A H 0.2800 0.9654 0.1874 0.269 Uiso 1 1 calc R
H9B H 0.1495 0.8978 0.2677 0.269 Uiso 1 1 calc R
H9C H 0.1487 0.9256 0.1280 0.269 Uiso 1 1 calc R
C10 C -0.1770(11) 0.6203(10) 0.0873(11) 0.164(5) Uani 1 1 d .
H10A H -0.1147 0.6482 0.0154 0.197 Uiso 1 1 calc R
C11 C -0.2325(9) 0.7516(9) 0.0620(10) 0.160(4) Uani 1 1 d .
H11A H -0.3143 0.7614 0.0131 0.240 Uiso 1 1 calc R
H11B H -0.1625 0.8155 0.0193 0.240 Uiso 1 1 calc R
H11C H -0.2597 0.7699 0.1357 0.240 Uiso 1 1 calc R
C12 C -0.2305(9) 0.5185(10) 0.0489(8) 0.140(4) Uani 1 1 d .
H12A H -0.3126 0.5537 0.0015 0.210 Uiso 1 1 calc R
H12B H -0.2567 0.4428 0.1174 0.210 Uiso 1 1 calc R
H12C H -0.1596 0.4879 0.0010 0.210 Uiso 1 1 calc R
C13 C 0.1000(5) 0.2761(5) 0.3979(5) 0.0594(14) Uani 1 1 d .
H13A H 0.1898 0.2665 0.4398 0.071 Uiso 1 1 calc R
C14 C 0.1047(7) 0.1737(6) 0.3283(6) 0.0867(19) Uani 1 1 d .
H14A H 0.1806 0.1948 0.2691 0.130 Uiso 1 1 calc R
H14B H 0.0162 0.1783 0.2889 0.130 Uiso 1 1 calc R
H14C H 0.1202 0.0828 0.3825 0.130 Uiso 1 1 calc R
C15 C -0.0189(6) 0.2451(6) 0.4920(6) 0.087(2) Uani 1 1 d .
H15A H -0.0203 0.3112 0.5353 0.131 Uiso 1 1 calc R
H15B H -0.0039 0.1545 0.5470 0.131 Uiso 1 1 calc R
H15C H -0.1079 0.2501 0.4534 0.131 Uiso 1 1 calc R
C16 C 0.2772(6) 0.4220(6) 0.5576(5) 0.0671(15) Uani 1 1 d .
H16A H 0.3553 0.4045 0.6113 0.101 Uiso 1 1 calc R
H16B H 0.2303 0.3377 0.5667 0.101 Uiso 1 1 calc R
H16C H 0.2113 0.4869 0.5765 0.101 Uiso 1 1 calc R
C17 C 0.4343(5) 0.3468(5) 0.3724(4) 0.0497(12) Uani 1 1 d .
C18 C 0.4413(5) 0.3409(6) 0.2575(5) 0.0669(15) Uani 1 1 d .
H18A H 0.3909 0.4062 0.1983 0.080 Uiso 1 1 calc R
C19 C 0.5192(6) 0.2430(6) 0.2272(5) 0.0730(16) Uani 1 1 d .
H19A H 0.5206 0.2399 0.1484 0.088 Uiso 1 1 calc R
C20 C 0.5964(5) 0.1479(5) 0.3127(5) 0.0583(14) Uani 1 1 d .
C21 C 0.5934(5) 0.1535(5) 0.4264(5) 0.0644(15) Uani 1 1 d .
H21A H 0.6464 0.0898 0.4847 0.077 Uiso 1 1 calc R
C22 C 0.5132(5) 0.2522(5) 0.4562(5) 0.0585(13) Uani 1 1 d .
H22A H 0.5120 0.2552 0.5350 0.070 Uiso 1 1 calc R
C23 C 0.6819(7) 0.0414(7) 0.2781(6) 0.0802(18) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C16 P1 C17 104.4(2)
C16 P1 C1 105.8(2)
C17 P1 C1 103.2(2)
C2 C1 C6 118.7(5)
C2 C1 P1 116.9(4)
C6 C1 P1 124.4(4)
C3 C2 C1 118.9(5)
C3 C2 C7 118.3(5)
C1 C2 C7 122.8(5)
C2 C3 C4 123.4(5)
C3 C4 C5 117.2(5)
C3 C4 C10 121.3(7)
C5 C4 C10 121.5(7)
C6 C5 C4 122.5(6)
C5 C6 C1 119.2(5)
C5 C6 C13 117.9(5)
C1 C6 C13 122.9(4)
C8 C7 C9 110.3(7)
C8 C7 C2 111.8(5)
C9 C7 C2 114.2(6)
C12 C10 C11 125.2(8)
C12 C10 C4 117.9(7)
C11 C10 C4 116.9(8)
C6 C13 C14 111.6(5)
C6 C13 C15 111.0(4)
C14 C13 C15 110.6(5)
C18 C17 C22 117.7(5)
C18 C17 P1 119.6(4)
C22 C17 P1 122.1(4)
C19 C18 C17 121.7(5)
C18 C19 C20 119.8(5)
C21 C20 C19 119.5(5)
C21 C20 C23 121.3(5)
C19 C20 C23 119.2(5)
C20 C21 C22 120.2(5)
C21 C22 C17 121.1(5)
F1 C23 F3 106.1(6)
F1 C23 F2 106.9(6)
F3 C23 F2 103.9(5)
F1 C23 C20 113.3(5)
F3 C23 C20 113.5(6)
F2 C23 C20 112.5(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C16 1.821(5)
P1 C17 1.833(5)
P1 C1 1.847(5)
F1 C23 1.289(7)
F2 C23 1.324(7)
F3 C23 1.312(7)
C1 C2 1.403(7)
C1 C6 1.412(7)
C2 C3 1.370(8)
C2 C7 1.523(8)
C3 C4 1.371(9)
C4 C5 1.381(8)
C4 C10 1.523(9)
C5 C6 1.372(7)
C6 C13 1.516(7)
C7 C8 1.451(10)
C7 C9 1.487(10)
C10 C12 1.388(11)
C10 C11 1.384(11)
C13 C14 1.524(8)
C13 C15 1.529(8)
C17 C18 1.375(7)
C17 C22 1.379(7)
C18 C19 1.358(7)
C19 C20 1.384(7)
C20 C21 1.360(7)
C20 C23 1.491(8)
C21 C22 1.373(7)
